This invention generally pertains to heterocyclic carbon compounds having drug and bioaffecting properties and to their preparation and use. In particular, the invention is concerned with oxazole derivatives characterized by Formulas I and II, infra., which are inhibitors of blood platelet aggregation.
The following chemical literature and patents are illustrative of related oxazole prior art known to applicant.
D. L. Aldous, et al., J. Org. Chem., 25, 1151 (1960) describe the chemistry of styryloxazoles of the formula ##STR2## wherein R is hydrogen, p-methoxy, o-hydroxy and 3,4-methylendioxy.
Brown, U.S. Pat. No. 3,578,671 describes a class of oxazole-2-polycarbon aliphatic monocarboxylic acids arylated at the 4- and/or 5-position in the oxazole ring of the formula ##STR3## in which each of the substituents R.sup.2 and R.sup.3 is a member of the group consisting of unsubstituted phenyl, naphthyl, thienyl and furyl radicals and phenyl radicals substituted by substituents selected from the group consisting of halogen, lower alkyl, lower alkoxy, nitro and trifluoromethyl radicals; and wherein R.sup.1 is selected from the group consisting of carboxyalkyl- and carboxylalkenyl radicals each containing from 2 to 5 carbon atoms and the amides, hydroxamic acid derivatives, lower alkyl esters and lower alkanoyloxy-lower-alkyl esters thereof. The compounds of U.S. Pat. No. 3,578,671 include the clinically effective anti-inflammatory agent known generically as oxaprozin (R.sup.2 =R.sup.3 =phenyl, R.sup.1 =(CH.sub.2).sub.2 CO.sub.2 H).
Meanwell, et al., U.S. Pat. No. 4,775,674 describe a series of 2,3-dihydro-2-oxo-1H-imidazo[4,5-quinolinyl ether derivatives of the formula ##STR4## wherein inter alia R.sub.1 and R.sub.2 are hydrogen, and "alk-Y" an alkanoic acid and ester residue. The compounds of U.S. Pat. No. 4,701,459 have cyclic AMP phosphodiesterase inhibitor activity and are useful as inhibitors of blood platelet aggregation and/or as cardiotonic agents.
Lautenschlager, et al., U.S. Pat. No. 4,460,598 issued Jul. 17, 1984 describe a series of triphenylis imidazol-2-yloxyalkanoic acids having the formula ##STR5## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 each are H, halogen, alkyl, alkoxy and trifluoromethyl; n is an integer of 1 to 10 and R.sup.7 is H, alkali metal ions, alkyl or benzyl group. The compounds of U.S. Pat. No. 4,460,598 are reportedly useful in the treatment of thromboembolic, inflammatory and/or atherosclerotic disease in man. A particularly preferred member of the series wherein R.sup.1 to R.sup.6 is hydrogen, n is 7 and R.sup.7 is sodium (identified in the art as octimibate sodium) has been described as possessing anti-aggregator activity and is under clinical development as an antihyperlipidemic agent.